Sodium hydride → HCID 86642311, compound

HRID 906000Notes

Reaction equation

HRID 906000 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([Cl:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([Cl:11])=[CH:9][N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 401522632-Bromo-7-chloro-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 86642311HCID 86642311, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

impure 2-Bromo-7-chloro-5H-pyrrolo[2,3-b]pyrazine was dissolved in DMF (30 mL). NaH (60%, 436 mg, 10.9 mmol) was added slowly. After the addition was complete stirring was continued for 30 minutes at RT. (2-Chloromethoxy-ethyl)-trimethyl-silane (1.9 mL, 10.9 mmol) was added and the reaction mixture was allowed to warm up overnight. The reaction was quenched with H2O. The aqueous layer was extracted with EtOAc. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 2.62 g of 2-bromo-7-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a yellow liquid (79% yield for 2 steps).

Workup

  1. additionAfter the addition
  2. temperatureto warm up overnight
  3. customThe reaction was quenched with H2O
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0-35% EtOAc)

Sources & evidence

ORD record
ord-066b449469814f22845ca62154fc2391
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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